You’re Never Too Old—or Too Successful—to Need a Mentor

Recently, I had lunch with an accomplished and slightly older CEO who had served as board chair of the corporation at which I had my first senior position. Not having seen him in years, I was delighted to catch up. But I was exhilarated when he expressed personal interest in my career, observed my success and challenged me to reach higher. Upon parting, I blurted out an awkward gratitude: “Thank you so much for your advice. It was so great to get, as all my mentors have died.”

Upon reflection later, it hit me that it was true. I have had a phenomenally successful and blessed career. Recently, I have written a successful book and feel I have made a difference on some big national issues. I still push myself harder than anyone else can – with one exception: My wife, a surgeon, pushes harder and lives by the mantra, “you can sleep when you die.” Unlike her, I need sleep.

Lately, however, I’ve felt the void of not having honest advice, feedback and encouragement to push me higher. Other than my wife and a few close friends, I am – and have been for a few years – mentor-less.

Any successful CEO can point to mentors along the way who made a difference in his or her career. I have been blessed with several. It is equally as rewarding and natural to want to give back and select those inside and outside your organization to mentor yourself.

But what about when you are at the top? The challenge that I face as a CEO is where to go for truly honest, helpful advice about me, rather than the entity I run. Of course, the first line for entity advice is trusted and savvy board members, and top employees whose wisdom I value. But both directors and executives have corporate roles that may limit candor on non-corporate issues. In my job heading a major national association of technology companies, I find myself more often serving as a sounding board for industry CEOs, providing candid career and corporate governance advice; yet it is probably not appropriate for me to seek similar advice from one who owes a fiduciary duty to my company.

Other CEOs are a great option – but the difficulty is in finding those professional peers with whom you have a rapport that goes beyond talking shop. Not surprisingly, finding others you can trust and with whom you can share your personal and professional weaknesses isn’t easy.

Some CEOs go to industrial psychologists, life coaches or executive specialists. Along the way, I found my brief sessions with each valuable in garnering kernels of insight, but all lacked the experience, insight or out-of-the-box thinking to do much more than observe, reflect and raise questions.

Several years ago I enjoyed a memorable dinner in Las Vegas with the two people whose advice I valued most: my father, Jerry Shapiro, and my mentor and friend, Jerry Kalov. I loved both men and will never forget that evening sharing stories and discussing life. Jerry Kalov, while running a public company himself and serving as my lead board member, told me that despite early successes, I would fail, and he would stand by me when I did. This allowed me to take risks, and of course many of these risks led to spectacular failures. He supported me, and I grew from each failure.

Sadly, within several months of that dinner, both Jerries passed. I often wonder, had I known their time was so limited, what questions I would have asked, what they would have said, and what advice they would have given. Even today, facing tough situations and decisions, I often ask myself: what would “Jerry” say?

As I counsel and mentor younger CEOs, I encourage them to never stop seeking guidance from others, even those not in their industry. After all, you never know what you can learn from a trusted outsider – someone whose only stake in your success or failure is based on pure friendship.

Above all, this means staying engaged. Continue making friends, look for others in your organization to mentor and never forget that you are where you are because someone helped you along the way.

Being mentored and mentoring is part of the life process of giving back. It might be lonely at the top, but it doesn’t have to be. Even for this lifelong learner, who knows that luck plays a role in life, I realize the amount I don’t know increases with my maturity.

I imagine many CEOs will share my experience of realizing that most of those who have helped us are gone. We can feel grateful that we knew them, and that they took the time to know us. But perhaps we can overcome the natural melancholy with this realization: We are never too old for mentoring, both as a mentor or as a recipient of a new friend’s advice.